Senior Account Executive, Insurance

Checkr • San Francisco, CA

2d • Hybrid

About The Position

Checkr Trust is building an entirely new business inside a category-defining company, focusing deeply on the insurance industry. This role offers a unique opportunity to accelerate solutions that detect bad actors before they impact businesses. While there is early traction and strong product-market pull in the insurance space, the business is still in its growth phase. This is a challenging, high-ownership role for someone who thrives in ambiguity, values accountability, and seeks long-term impact. It is not a passive role managing inbound leads, but rather a territory-building, market-educating, and full-cycle ownership position within the insurance vertical, operating with the resources of an established company.

Requirements

• 5–7+ years of full-cycle, quota-carrying sales experience — hunting required
• Deep roots in the insurance industry
• Sold six- or seven-figure deals in complex, multi-stakeholder environments
• Understands insurance workflows well enough to connect Checkr Trust's solutions to real underwriting and risk management problems
• Has built pipeline when there was no brand awareness in a market
• Worked in a startup or operated like you were in one
• Outperformed targets in situations that weren't perfectly set up for you
• Tangible examples of projects created using advanced AI tactics
• Carries an A-player mindset: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes
• Has grit. Your energy and work ethic raises the bar of others
• Prefers autonomy and ownership to rigid structure
• Doesn't wait for perfect messaging — you test, iterate, refine
• Comfortable hearing "no" repeatedly without losing momentum
• Cares about building something meaningful, not just closing this quarter's deal
• Holds yourself to a higher internal standard than anyone else will
• People describe you as relentless, disciplined, competitive — but collaborative
• Understands that building something valuable in a complex, regulated industry like insurance is both rewarding and uncomfortable

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms — then build repeatable motion where none exists yet
• Leverage existing insurance relationships to accelerate pipeline and shorten deal cycles
• Own the entire deal lifecycle — from cold outreach to multi-threaded enterprise close
• Educate the market on a category that is still forming, translating Checkr Trust's value into the language of underwriting, loss prevention, and claims risk
• Navigate complex insurance buying processes involving underwriting, compliance, legal, and executive stakeholders
• Experiment with AI to find efficiencies across your work
• Partner cross-functionally with product, legal, operations, and leadership to shape how we win in insurance
• Hit ambitious revenue targets

Benefits

• Learning and development allowance
• Competitive cash and equity compensation, and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend
• Lunch five times a week
• Commuter stipend
• Relocation stipend may be available

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed